While the Submariner was our top pick for a Rolex sport watch, the Datejust II is our top pick for a Rolex dress watch. Updated from 36mm wide to 41mm wide, the famous fluted bezel of the Datejust has been a hallmark of Rolex for decades. At first, the Rolex Datejust might seem stuffy and conservative, but it is a remarkably useful and good looking watch once you get to know it. In steel with a white gold bezel, its base price is about $9,000. Though, in precious metals, it can go way up in price. A perfect watch with a suit that combines a good style and the name you are looking for.